US7677315B2 - Degradable surfactants and methods for use - Google Patents
Degradable surfactants and methods for use Download PDFInfo
- Publication number
- US7677315B2 US7677315B2 US11/244,345 US24434505A US7677315B2 US 7677315 B2 US7677315 B2 US 7677315B2 US 24434505 A US24434505 A US 24434505A US 7677315 B2 US7677315 B2 US 7677315B2
- Authority
- US
- United States
- Prior art keywords
- degradable
- surfactant
- acid
- group
- poly
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
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- 238000000034 method Methods 0.000 title claims abstract description 72
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- 239000002253 acid Substances 0.000 claims abstract description 76
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- 230000000593 degrading effect Effects 0.000 claims abstract description 7
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- 125000000217 alkyl group Chemical group 0.000 claims description 25
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- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 229920000805 Polyaspartic acid Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003254 anti-foaming effect Effects 0.000 description 1
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- 239000008346 aqueous phase Substances 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 238000003491 array Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GDFLGQIOWFLLOC-UHFFFAOYSA-N azane;2-hydroxypropanoic acid;titanium Chemical compound [NH4+].[Ti].CC(O)C([O-])=O GDFLGQIOWFLLOC-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 229910001570 bauxite Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 231100000693 bioaccumulation Toxicity 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910010293 ceramic material Inorganic materials 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910021540 colemanite Inorganic materials 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 229920006237 degradable polymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- RDMZIKMKSGCBKK-UHFFFAOYSA-N disodium;(9,11-dioxido-5-oxoboranyloxy-2,4,6,8,10,12,13-heptaoxa-1,3,5,7,9,11-hexaborabicyclo[5.5.1]tridecan-3-yl)oxy-oxoborane;tetrahydrate Chemical compound O.O.O.O.[Na+].[Na+].O1B(OB=O)OB(OB=O)OB2OB([O-])OB([O-])OB1O2 RDMZIKMKSGCBKK-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000010881 fly ash Substances 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000007849 furan resin Substances 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
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- 125000001165 hydrophobic group Chemical group 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002506 iron compounds Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- 150000002772 monosaccharides Chemical group 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- XZZXKVYTWCYOQX-UHFFFAOYSA-J octanoate;tin(4+) Chemical compound [Sn+4].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O XZZXKVYTWCYOQX-UHFFFAOYSA-J 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000010452 phosphate Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 description 1
- 229940065514 poly(lactide) Drugs 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical class [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- DPUZPWAFXJXHBN-UHFFFAOYSA-N tetrasodium dioxidoboranyloxy(dioxido)borane Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]B([O-])OB([O-])[O-] DPUZPWAFXJXHBN-UHFFFAOYSA-N 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
- 229910021539 ulexite Inorganic materials 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/602—Compositions for stimulating production by acting on the underground formation containing surfactants
- C09K8/604—Polymeric surfactants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/16—Amines or polyamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/18—Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/66—Compositions based on water or polar solvents
- C09K8/68—Compositions based on water or polar solvents containing organic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/72—Eroding chemicals, e.g. acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/60—Compositions for stimulating production by acting on the underground formation
- C09K8/62—Compositions for forming crevices or fractures
- C09K8/72—Eroding chemicals, e.g. acids
- C09K8/74—Eroding chemicals, e.g. acids combined with additives added for specific purposes
Abstract
Description
wherein R1 is a hydrogen, alkyl, aryl, alkylaryl, acetyl, or heteroatoms; R2 is a hydrogen, alkyl, aryl, alkylaryl, acetyl, or heteroatoms; R3 is hydrogen, alkyl, aryl, alkylaryl, acetyl, alkoxyl, benzoyl, or heteroatoms; or a group comprising an anionic group, a cationic group, or a non-ionic group; R4 is a group such as H, Na, K, or Li, or a group comprising an anionic group, a cationic group, or a non-ionic group; m can be an integer between 1 and 20; and X can be an integer between 2 and 100. The above formula represents a non-limiting example of a suitable degradable surfactant and numerous other embodiments of degradable surfactants are suitable for use in the present invention.
In one embodiment, a suitable graft copolymer surfactant may comprise a hydrophilic polymeric backbone having branches of a hydrophobic degradable polymeric block along its length, for example, guar grafted with polylactic acid or poly(caprolactone). In another embodiment, a suitable graft copolymer surfactant may comprise a hydrophobic degradable polymeric backbone having branches of a hydrophilic polymer along its length.
wherein R1 is a methylene chain of from 1 to 4 carbons, alkyl, hydroxyl alkyl, ethoxylated alkyl, or arylalkyl group; R2 is an alkyl, hydroxyl alkyl, ethoxylated alkyl, or arylalkyl group; R3 is an alkyl, hydroxyl alkyl, ethoxylated alkyl, or an arylalkyl group; R4 is an alkyl, hydroxyl alkyl, ethoxylated alkyl, or an arylalkyl group; and X is a chlorine, bromine, iodine, ½SO4, HSO4, CH3SO3, or the like. A and B may be hydrophilic and hydrophobic degradable polymeric blocks, respectively, as described previously.
wherein R1 is a methylene chain of from 1 to 4 carbons, alkyl, hydroxyl alkyl, ethoxylated alkyl, or arylalkyl group; R2 is an alkyl, hydroxyl alkyl, ethoxylated alkyl, or arylalkyl group; R3 is an alkyl, hydroxyl alkyl, ethoxylated alkyl, or an arylalkyl group; R4 is an alkyl, hydroxyl alkyl, ethoxylated alkyl, or an arylalkyl group; R5 is a methylene chain of from 1 to 4 carbons, alkyl, hydroxyl alkyl, ethoxylated alkyl, or arylalkyl group; X is a chlorine, bromine, iodine, ½SO4, HSO4, CH3SO3, or the like. A and B may be hydrophilic and hydrophobic degradable polymeric blocks, respectively, as described previously.
TABLE 1 |
Sample Degradable Block Copolymer Surfactants |
Sample | Block Copolymer | Mn (Daltons) |
Copolymer Surfactant No. 1 | mPEG-b-PLA | 5000-5000 |
Copolymer Surfactant No. 2 | mPEG-b-PLA | 5000-3000 |
Copolymer Surfactant No. 3 | mPEG-b-PLA | 5000-1500 |
Copolymer Surfactant No. 4 | mPEG-b-PLA | 350-2000 |
Copolymer Surfactant No. 5 | mPEG-b-PLA | 2000-5000 |
Copolymer Surfactant No. 6 | mPEG-b-PCL | 350-1500 |
Copolymer Surfactant No. 7 | mPEG-b-PCL | 350-2000 |
TABLE 2 |
Foam Water Drainage |
Time | Water Drainage (mL): Copolymer | Water Drainage (mL): |
(min) | Surfactant No. 2 Foam | PLURONIC ® F108 Foam |
1 | 80 | 50 |
2 | 150 | 120 |
3 | 250 | 170 |
4 | 380 | 320 |
5 | 400 | 345 |
6 | 410 | 360 |
7 | 422 | 375 |
8 | 430 | 385 |
9 | 438 | 395 |
10 | 445 | 402 |
TABLE 3 |
Sample Composition |
Component | Sample 1 | Sample 2 | ||
Water (mL) | 79 | 79 | ||
Copolymer Surfactant No. 1 (g): | — | 5.6 | ||
mPEG-b-PLA (Mn 5000-5000) | ||||
Copolymer Surfactant No. 5 (g): | 4 | — | ||
mPEG-b-PLA (Mn 2000-5000) | ||||
HMP ™ Gelling Agent (mL) | 20 | 20 | ||
Calcium Carbonate (g) | 2 | 2 | ||
Sodium Tetraborate (mL) | 1 | 2 | ||
TABLE 4 |
CO2 Gas Generation |
CO2Volume (mL) |
Time (hr) | Sample 1 | Sample 2 |
0 | 0 | 0 |
5 | 20 | 55 |
10 | 42 | 68 |
15 | 68 | 104 |
20 | 90 | 118 |
25 | 100 | — |
30 | 118 | — |
Claims (33)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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US11/244,345 US7677315B2 (en) | 2005-05-12 | 2005-10-05 | Degradable surfactants and methods for use |
PCT/GB2006/003575 WO2007039710A1 (en) | 2005-10-05 | 2006-09-26 | Degradable surfactants and methods for use |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US11/128,060 US7662753B2 (en) | 2005-05-12 | 2005-05-12 | Degradable surfactants and methods for use |
US11/244,345 US7677315B2 (en) | 2005-05-12 | 2005-10-05 | Degradable surfactants and methods for use |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/128,060 Continuation-In-Part US7662753B2 (en) | 2005-05-12 | 2005-05-12 | Degradable surfactants and methods for use |
Publications (2)
Publication Number | Publication Date |
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US20060254774A1 US20060254774A1 (en) | 2006-11-16 |
US7677315B2 true US7677315B2 (en) | 2010-03-16 |
Family
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/244,345 Expired - Fee Related US7677315B2 (en) | 2005-05-12 | 2005-10-05 | Degradable surfactants and methods for use |
Country Status (2)
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US (1) | US7677315B2 (en) |
WO (1) | WO2007039710A1 (en) |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20090186761A1 (en) * | 2008-01-18 | 2009-07-23 | Cleareso, Llc | Use of bio-derived surfactants for mitigating damage to plants from pests |
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